Magnesium, chloro-1H-pyrrol-2-yl-

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• Chemical Name: Magnesium, chloro-1H-pyrrol-2-yl-
• CAS No.: 116751-23-6
• Molecular Formula: C4H4ClMgN

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A MILD METHOD FOR THE SYNTHESIS OF 2-KETOPYRROLES FROM CARBOXYLIC ACIDS

10.1016/S0040-4039(01)83003-3

The study presents a mild and efficient method for synthesizing 2-ketopyrroles from carboxylic acids. The key chemicals involved in this synthesis are 2-pyridylthiolesters and pyrrylmagnesium chloride. The process begins with the conversion of a carboxylic acid to a 2-pyridylthiolester using 2,2'-dipyridyl-disulfide and triphenylphosphine in toluene at 25°C under an argon atmosphere. Subsequently, pyrrylmagnesium chloride is added at -78°C, leading to the formation of the 2-ketopyrrole product. This method is notable for its mildness, selectivity, and efficiency, making it suitable for the synthesis of complex polyfunctional molecules. The study demonstrates the versatility of this method by synthesizing various 2-ketopyrroles, including those derived from biologically active molecules such as pinanethromboxane A2, prostaglandin F2a, and monensin. The synthesized 2-ketopyrroles are isolated in excellent yields using techniques like preparative layer chromatography or flash column chromatography.

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